May or may not be a good teacher, but never a good disciplinarian. Often let students call them by their first name ("Mr. Hippie Teacher is my father; you can call me Rod"). Definitely Truth in Television; many people had art teachers like this. While in fiction they can teach any subject, art teachers, guidance counselors and other teachers of "soft" or "creative" subjects tend to predominate with hard sciences being less common unless crossed with Absent-Minded Professor. When portrayed sympathetically, this character is usually a Cool Teacher. If portrayed unsympathetically, they're well-meaning but ultimately incompetent pushovers who are viewed as A factories by students at best and arrogant, passive-aggressive moralists who hand out As to anyone who agrees with them at worst.

In Animal House, Donald Sutherland plays Professor Dave Jennings, a university level version of this. In a slight variation, the film's setting is contemporaneous with the actual hippie movement, making him a Cool Teacher as well. As it turns out, he's just as bored by the subject matter of his lectures as his students are.

Literature

Barbara Finney from The Cat Ate My Gymsuit was the first person to help insecure Marcy Lewis break out of her shell. Her controversial teaching methods has also caused an uproar from a large portion of the school faculty.

Although not actually hippieish, Madame Frout, headmistress of the Frout Academy of Learning Through Play in the Thief Of Time, has invented a method of teaching that doesn't involve dicipline because she wasn't any good at it. Her best teacher, Susan Sto Helit, completely ignores it.

Earth Mother (her codename), one of the Magical Arts instructors at Whateley Academy in the Whateley Universe. She was a 'flower power' superheroine in the 60's.

Mr. Freeman, the art teacher from the YA book Speak (although the narrator takes pains to point out that he's not an ineffectual disciplinarian; he has different rules than the other teachers, but he does make people follow them).

Ms Partridge, Bigmac's social worker in the Johnny Maxwell Trilogy used to be like this, before dealing with Bigmac wore her down:

When she'd started the job, less than a year ago, she'd firmly believed that everything that was wrong with the world was the fault of Big Business and the Government. She believed even more firmly now that it was all the fault of Bigmac.

Mrs. Hiolet in Tough Magic is described as being bubbly, overly-bright and friendly, with strict views against corporal punishment.

iCarly: Mr. Henning. He loves nature, disproves of modern methods (or rather just major energy wasting ones), and takes students on a root and berry retreat.

Spencer: You know, when I was at Ridgeway, I had a teacher who was such a loser! He's a freaky weirdo and smells like rotten wood...

Mr. Henning: Spencer? That's me.

Spencer: What? (pauses) Oh.

Henning seems to use the root and berry retreat as a form of Cool and Unusual Punishment on his students. While he himself enjoys it, he knows his students don't and uses it as a threat to make them try their best on their projects (failing grades can only be made up by going on the trip with him).

Interestingly enough, while he still fits the classic trope, he's also a well-rounded enough character to be legitimately helpful at times and be thoroughly capable of discipline.

Rosso (driving up to Lindsay and Daniel who are skipping school): Guesswho's in trouble!

Though he may be more disciplinary than most trope examples, the legacy of his time as a hippy does occasionally disadvantage him. For example, in an episode when then Vice President George H.W. Bush came to visit the school, despite his political differences he tied back his hair and put on his best air of respectability. However, he is turned away by a secret service agent (played by Ben Stiller) due to his name being on some subversive mailing lists back in The Sixties.

Art Cooney on The Wedge. He is of the "Call me Art" mould, and has zero respect from his students.

According to Paul Dinello, Jellineck (a totally insecure loser) was based on Hippie Teachers who in real life are often considered kind of creepy by their students, who don't really want a forty-year-old man giving them advice on problems he shouldn't even know about and insisting that he "gets" them all the time.

Ms. Dawes of Degrassi is this, she is the art teacher. She also happens to LARP in her spare time.

Mr. Donovan of Square Pegs, who dressed conservatively but would hark back to his nostalgic days of sit-ins and experimental theater.

J.D. becomes a bit like this in Scrubs: Med School (season 9). "Let's gather round the Teaching Tree!"

Valerie on Awkward., who is more of a Cloud Cuckoolander than a hippie, but fits the mold by being a horrible disciplinarian and treating the kids (especially Jenna, her favorite) like they're her friends.

Video Games

Professor Potsdam in Magical Diary, although she can be terrifyingly competent when the need calls for it. All while calling you and the other students such things as "starshines" and various diminuitives for plant and animal offsprings.

Web Comics

Merlin Ambrosius, in his role as Arthur's art teacher in Arthur, King of Time and Space ... maybe. He's definitely a hippy and a teacher, but we don't really see him teach to judge if he actually fits the trope.

Western Animation

Mr. Van Driessen on Beavis And Butthead (pictured). Supposedly based on a real teacher Mike Judge had in high school.

Mr. Mackey, the school counselor on South Park, is almost a Captain Ersatz for Mr. Van Driessen, since he is constantly using the catchphrase "Mmmkay?" He doesn't quite fit the profile visually with his tightly-tied tie and short haircut, but he is a lot more "empathetic" toward the children than teacher Mr. Garrison (who often loses his temper when the students get unruly). His Day In The Spotlight episode also has him briefly take up drugs and embrace an overtly hippie lifestyle, although of course he gives up both by the end of the episode.

Mr. O' Neill on Daria, who is scarily similar to Mr. Van Driessen save for the fact that he's not overtly a hippie. When Daria and Jane come to visit his apartment in one episode, it's filled with new age-y paraphernalia, and he offers them tea with a gem tincture.

Mr. Simmons in Hey Arnold!; like Mr. Mackey he's more well-dressed than a stereotypical hippie, but definitely has the attitude.

Recess: Ms. Grotke is the most obvious example, but according to The Movie, Principal Prickly and Ms. Finster were Hippie Teachers back in the sixties.

Doug's school counselor Mr. Shellacky straddles this and Misplaced Kindergarten Teacher. As that he is always suggesting "Hugs" and other "Make Love" solutions to problems, his office is plastered with feel-good posters, and he looks vaguely like a caricature of Bob Dylan in an ugly sweater.

Springfield Elementary has one — he's just a background character, but he usually shows up when there's a group of teachers onscreen. When all the textbooks were stolen and the teachers had to improvise their lessons, he sat cross-legged on his desk and asked, "Did I ever tell you kids about the '60s?"

Steve Small from The Amazing World of Gumball is the student counselor for Elmore Junior High and very much a hippie: he wears tie-die and sandals, holds interpretive dance classes, and tried to subsist on a diet of sunlight and meditation. Beneath that however, he strongly diverges from the type as he shows himself to be violently bipolar, impatient, and often quite mean to his students—he once smashed an old painting with a club and burned it for being a "relic of convention", acted as a Drill Sergeant Nasty at cheerleading try outs, and when two students have trouble with when to tell the truth or lie he eventually decides to just scare them into never talking again.

If someone was a 20 year old college student in the 1960s, then today they'd be old enough to retire. Which means many, if not most of them likely entered the workforce after graduating college. Thanks to the Draft being a big part of the 60's and 70's as well, it's entirely possible for one of your teachers to have been a Hippie Teacherand a Retired BadassVeteran Instructor.

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